


such a roller coaster (and a killer queen you are)

by gaypanic



Category: Once Upon a Time (TV)
Genre: Adventure, Alternate Universe, F/F, Fluff, Mistaken for Being in a Relationship, Road Trip, bed sharing, hitchhiker!regina, no magic, pretending to be a couple sometimes, they are probably late twenty-something's i guess, travelling, trucker AU, trucker!emma
Language: English
Status: In-Progress
Published: 2019-01-21
Updated: 2019-01-28
Packaged: 2019-10-14 03:42:45
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 13,377
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17500880
Author URL: https://archiveofourown.org/users/gaypanic/pseuds/gaypanic
Summary: Emma is a trucker on a cross country mission for Create-A-Cuddly, Inc. when she comes across a hitchhiker on the run from her troubles. She decides to help the woman, and it turns into the road trip of a lifetime.[a swan queen trucker au]





	1. Day One

**Author's Note:**

  * For [parrillayeah](https://archiveofourown.org/users/parrillayeah/gifts).



> this is the first fic prompt i ever received, from one of my all time greatest friends, and i thought it would make a good gift for her birthday. THIS IS FOR YOU BAB. i hope you like it. 
> 
> mAJOR thank you to my incredible beta, laura, who is more patient with me than i probably deserve
> 
> title from “rollercoaster” by bleachers. it’s an amazing song, so you should give it a listen, either jack’s original, or the version sung by charli xcx. i also made a playlist for this fic, which can be found [HERE](https://open.spotify.com/user/lamestories/playlist/0DQkCqudQYlrIJPxMw3fVG?si=ZxI7krKVQRGoHREDxk6T0Q)
> 
>  
> 
> _(updates will be every monday/friday unless otherwise specified)_
> 
>  
> 
> (disclaimer: regarding certain details, please note that some things i intentionally bent to my will, such as the amount of fuel emma’s truck carries and how infrequently she has to refuel, and probably her job timeline in general. some of the locations they visit may also have inaccuracies, but i did what i could for someone who has never been to any of them)

"Emma, welcome to the team." 

 

The blonde grins as she shakes the hand of her new boss. His voice is gruff and his hand is calloused, but she supposes he’s nice enough. She glances nervously at August and Neal, both giving her a thumbs up from the side, which would have been more encouraging if her boss didn’t disappear only two seconds later, muttering under his breath.

 

“Don’t worry, okay? That’s just how Leroy is. He’s been in this business for years, and I think it’s hardened him. He’s not as nice as he used to be, but that might be the alcohol,” August shrugs. “Either way, he seems to like you.”

 

“How do you know?” Emma asks, more than a little skeptical at her friend’s opinion.

 

“He hasn’t fired you yet,” Neal offers with a sound that could pass for a laugh if Emma doesn’t think too hard about it. “He’s letting you drive, which is more than most people seem to get.”

 

“Yeah,” Emma snorts. “A _cross-country_ trip for _Create-A-Cuddly_. Like that means anything.”

 

“Actually it does,” August says. “It only sounds terrible because that’s the kind of job no one wants. But even so, it’s not easy to drive across the country and back for a load, so really, this is like a test.”

 

“What if I fail?”

 

“You won’t. Remember, you passed all the official tests and classes. Your license checks out. You’re cleared to be a trucker, and for Leroy, that means you’re good to go. Failing in his eyes includes firing you before giving you a shot, which, you’ve already gotten. Trust us, you’re _fine._ ”

 

Emma nods, deciding to trust the two friends that got her into this business to begin with. It isn’t the best paying job, but it is certainly more than she was making at Chuck’s Chicken, so she lets Neal and August lead her into their trucker lives, under the management of the grumpiest person the blonde has ever met.

 

 _It could be worse_ , she figures, as she gets her truck ready to head out to pick up the shipment. She logs her time of departure, 8:57am; her place of departure, Boston, MA; her pick-up location, Los Angeles, CA; and her shipment product, miscellaneous parts and supplies for Create-A-Cuddly, Inc. She double checks her paperwork, confirms that she has everything she needs to make the trip, and takes a deep breath as she shifts her truck into gear and pulls out onto the road.

 

Since it’s her first trip, she only _thinks_ she knows what to expect, but when it comes down to it, she doesn’t fully realize what she’s getting herself into. It’s the kind of thing you can think about and imagine in great detail, but have no understanding of until you’re actually in the situation, wondering why your expectations for it were so misplaced.

 

This is where Emma finds herself as she approaches her fifth hour of driving, right after making her first pit stop. She’d been excited so far, until she’d refueled, bought an energy drink and a candy bar and started driving again. It didn’t take long for her to realize how _lonely_ it all was, and how much she missed just being in one place.

 

She blasts the radio for a little while longer, and she even gives audiobooks a try, but still, four hundred and fifty miles later, she can’t shake the realization that she isn’t cut out to be a trucker. She’ll stay strong enough for as long as she has to, of course, but that doesn’t mean she has to _like_ it.

 

By the time she’s gone seven hours, Emma feels like she’s had more than enough, but it’s only four pm, and she hasn’t even left the state of New York. How does she plan to make it to _Los Angeles_ and back if she can hardly stand the time it took her to get to _Buffalo_. She groans as she pulls up to a truck stop to refuel, and she goes against August’s advice and gets herself another energy drink despite the late hour. She also buys one of those gas station hot dogs that are usually never as good as they look, and she’s surprised when it isn’t actually half bad.

 

She heads back out again, doing everything she can to not calculate the mental math in her head of how much time she has remaining. Really, there isn’t much more she can do to entertain herself at this point, having tried all the stupid things Neal recommended before she even _passed_ Buffalo. She’s about an hour from pulling over for the night, when on a smaller road to get back on I-90, she spots a woman, who looks to be about her age, walking along with a backpack.

 

When Emma pulls over and rolls down the passenger window, she still isn’t sure it’s the best idea. August and Neal had warned her about hitchhikers, telling her it would be better in the long run if she were to ignore them and just go about her business. Emma had agreed with them at the time, understanding the logic behind their decision up until she saw this woman strolling along by herself. All Emma could think then is that _anyone_ could pick her up. What would happen if Emma didn’t?

 

So she stops.

 

“Hey!” Emma calls out the window, surprised the brunette hadn’t so much as looked her way as she approached. “You need a lift?”

 

“Thank god,” she thinks she hears the other woman mutter as she opens the door and pulls herself into the truck. “Where are you heading?” she asks next, and _that,_ Emma can hear.

 

She’s stunned for a moment, blinking a few times before the question actually registers. “LA,” she answers, and the girl nods before she’s even finished.

 

“Oh, great. Me, too. Thanks for the ride,” she says, dropping her bag at her feet and buckling up without so much as a glance at Emma.

 

The blonde is speechless at the other woman’s demeanor, and even more so by her appearance in general. She’s one of the most stunning people Emma is sure she’s ever laid eyes on, and the air of confidence she clearly has does her so many favors.

 

Eventually the brunette turns to Emma, her brows furrowed. “Well? Are we going or not?”

 

“I uh—” Emma starts, laughing as she turns back to look out the front window and back to the other woman. “You’re not worried about me being a murderer or something? I mean, you don’t even know my name.”

 

“Tell me your name then,” she demands, a little impatiently.

 

“Emma.”

 

“Nice to meet you, Emma. My name is Regina. Are you ready to go? You must have some sort of schedule to keep to if you’re driving all the way across the country, so I suggest we get a move on.”

 

Not appreciating being undermined, even if it is her first day on the job, Emma softly scoffs, holding back every ounce of sass she can and choosing not to say anything. Instead, she shifts the truck into gear and gets back on the road, heading toward I-90 once again.

 

She decides not to talk to Regina, especially not as long as the other woman has an attitude. However, the more time passes, the more curious she is about what Regina’s plans for LA are, especially if she’s choosing to hitchhike and jump in a truck with a random stranger instead of just buying a bus ticket. The brunette certainly doesn’t look like she’s scraping by. In fact, if Emma didn’t know any better, she would say Regina is actually really well-off, at least going by the brand of her backpack and her jacket. Probably her boots as well, but Emma can’t see them well enough to say for sure.

 

With every sign they pass, closer to leaving New York, Regina starts to get more antsy, fidgeting in her seat, giving Emma a few shifty glances, and even going so far as to bite her perfectly manicured nails. She’s only a couple miles away from the state line between New York and Pennsylvania, and Regina’s behavior makes the blonde want to slam on the breaks just to make her sweat.

 

Instead, she keeps driving, slowing minimally enough that Regina notices, but not so much that she would be a danger on the road. “What’s the deal?” she asks before Regina can comment. “About leaving New York?”

 

“There’s no _deal_ ,” Regina mumbles.

 

“Like hell there’s not,” Emma retorts, her voice coming out harsh until she realizes she may have hit a sore spot. Regina looks down, and when Emma speaks again, her voice is softer. “What are you running from?”

 

Her compassion goes unappreciated when the brunette snaps back at her. “What? You just assume I’m running from something just because I’m hitchhiking across the country? You don’t know the first thing about me.”

 

“You’re right,” the blonde replies through gritted teeth. “I don’t. But seeing as we’re stuck together for the next twenty-five hundred miles, we might as well get to know each other.”

 

Regina doesn’t say anything to that. Other than crossing her arms and staring out the passenger window, she gives no response. At least the fidgeting has stopped, for the most part. The brunette’s leg shakes, but she doesn’t move in her seat, and she definitely doesn’t glance at Emma. It’s _annoying_ , Emma thinks as she tries to make the most of this apparently shitty situation.

 

Sure, she could kick the woman out. There’s no reason why she _has_ to give her a ride. She’s not tied to her in any way or obligated to take passengers. Heck, she’s even encouraged not to. But there’s something about Regina that makes Emma want to do the right thing, even if this woman doesn’t deserve it.

 

That’s when Emma gets an idea.

 

It’s hard to be spontaneous when she doesn’t know exactly where to go—and she can’t just look it up while she’s driving—but with some help from road signs and a general memory of the area from her childhood, Emma manages to get them to the right place.

 

As Emma finds a place to park the truck, Regina finally loosens up (as in, she’s no longer jiggling her leg in the seat), and she turns to Emma looking almost alarmed. “Are you stopping so you can kick me out?”

 

The blonde can’t help but laugh at that. “No.”

 

“Then what are we doing here? Shouldn’t we stay on the road while there’s still some daylight?”

 

Emma shrugs. “I’ve decided I don’t like being on the road with a total stranger.”

 

“So you _are_ kicking me out,” Regina deadpans, glancing around the immediate area as if surveying it for spending the night.

 

“ _No_ ,” Emma repeats. “I’m not kicking you out.”

 

“But you said—”

 

“Yeah, I know what I said,” Emma says as she climbs out of the truck and shuts the door before going around to Regina’s side and opening it for her, since the brunette hadn’t budged. “I’m doing you a favor, alright? Just shut up and enjoy it.” She offers the other woman a wry smile as she extends her hand.

 

Regina takes it, and Emma tries not to show her surprise at how soft her skin is. “Technically two,” she mutters, and the blonde levels her with a look. The other woman groans as she drops her hand and crosses her arm. “ _Fine_ , I’ll be quiet.”

 

Wordlessly, Emma leads them from the parking lot toward the closest shore, taking in the cool breeze of the summer air. She turns to make sure Regina’s wearing her jacket, knowing it’s going to get chillier once the sun sets. They make it to the first beach, and she’s pleased to see that it isn’t very crowded.

 

“We’re here,” Emma announces as she turns back to the brunette, gesturing out toward Lake Erie. “I know you’ve probably seen it already, especially if you’re from the area I picked you up at, but it was the best I could do on such short notice.”

 

She’s a little embarrassed now that they’re actually standing here in the sand, damp from recent rain, staring off at the fog floating through the air while a kid screams in the distance, but despite it all, Regina looks awestruck as she takes in the sight before them.

 

“Regina?” Emma prompts, nudging the other woman lightly with her elbow.

 

“It’s…” she starts to respond, her voice catching in her throat until she clears it. “Why are we here?” she asks again, and Emma shrugs.

 

“I thought we could watch the sunset.”

 

“But _why_?” she tries again.

 

“I don’t know,” Emma says before sheepishly admitting, “You just seemed like you could use some peace in your life. This was the first idea I had.” Dark eyes lock with hers with a look so intense it makes Emma blush. She’s about to take back the entire idea, but she stops when Regina suddenly asks if she has a towel so they can sit down. She breaks into a grin. “Yeah, I’ll be right back. Don’t go anywhere, okay?”

 

“Where would I go?” Regina asks, rolling her eyes, but her voice lacks the same bite it did back in the truck, so the blonde keeps smiling as she jogs back to the truck.

 

As promised, Regina is exactly where Emma left her, and the blonde spreads out the towel and sits down. The other woman is soon to follow, eyeing Emma as she rummages through her bag, pulling out the two sandwiches she had in her small refrigerator, a couple bags of chips, and two bottles of water. “I thought you might be hungry,” Emma offers, and Regina gives her a smile, the first one since they met a few hours ago.

 

“Thanks,” she says, and the two fall into silence as they eat dinner and watch the sun start to set through the fog. It’s more beautiful than Emma imagined it would be. The sky’s colors aren’t as vibrant as they would be without the fog, but they light up softly behind the mist, subdued enough that the view doesn’t beg for attention, it just _is_.

 

The colors slowly fade, and eventually they disappear. Everything feels still for a long moment—the only noise coming from the wind as it blows through the trees nearby, and the soft sound of the water’s movements—before Regina speaks. “My mother works in New York—Manhattan. Running one of those businesses you always hear about, but you never know exactly what they do.”

 

Emma watches Regina as she talks, nodding along in the brief seconds that dark eyes meet hers.

 

“She’s the CEO, and she wants me to follow in her footsteps.”

 

“But you don’t want to?” Emma says more than she asks, and the other woman lets out a bitter laugh.

 

“Of course not.”

 

Taking in the new information, Emma nods along, contemplating her next question. It slips easily from her lips, but from the look in Regina’s eyes in response, it’s clear the brunette wasn’t expecting it. “What do you want to do?”

 

“I…” Regina starts, trailing off like she doesn’t know the answer. “I’ve never really thought about it. My whole life has been building towards taking the company. I haven’t had much of a chance to figure things out on my own.”

 

Emma leans back, making herself comfortable as she lies down. She’ll probably have sand in her hair, but she doesn’t mind. The moment is relaxing and perfect in a way she never expected this night to be. “Maybe I can help you figure it out,” she offers with a small shrug.

 

The silence lasts longer than the blonde expected it to, and she looks over at the other woman, a little worried until she sees dark eyes looking at her in surprise. “Why would you do that?” It makes Emma laugh, considering how many times Regina has asked _why_ since they’ve gotten here, but the brunette doesn’t laugh with her. “I’m serious, Emma. Why are you being so nice to me?”

 

The blonde shrugs, as much as she can since she’s lying on her back, but other than that, she isn’t sure what to say. Honestly, she doesn’t know _why_ . She just knows that she _is_. She contemplates her answer for another period of silence until Regina suddenly asks, “Did you always want to be a trucker?”

 

Emma laughs again through her surprise. “No,” she simply answers. “I never thought I would end up here, but money was tight, so…here we are.”

 

Regina hums in response before following Emma’s lead and asking, “What would you be doing if you weren’t a trucker?”

 

“I don’t know. I haven’t figured it out yet.” Regina nods as she looks back out at the lake, now only dimly lit by the moon’s soft light through the clouds. She smiles when she realizes how similar their situation is, at least at the core. “I guess it’s good we found each other then,” she concludes, so softly that she isn’t even sure she said it out loud. If Regina heard her, she doesn’t say anything, and the two fall back into a comfortable silence, relishing the cool breeze and each other’s company.

 

A few hours have passed since they arrived, and it’s nearly nine o’clock when Emma suggests they head out so they can find a good place to stop for the night. Regina offers to shake off the sandy towel while Emma figures out where they’ll spend the night be stopping, and soon after they’re back on the road.

 

It’s about a forty minute drive until they cross the state line into Ohio, and another fifteen minutes to a truck stop near Kingsville. She refuels while Regina finds a bathroom, and by the time the brunette gets back, Emma has the truck parked and ready to go for the night. “I hope you’re okay to stay with me for the night,” she casually says, turning away in time to miss Regina’s eyes widening.

 

“Stay _where_?” she asks, and Emma frowns as she turns around, immediately humored by the way that Regina starts looking around the truck stop.

 

“In my cabin,” Emma responds, fighting back a laugh. She gestures back at the truck. “I’ll show you.”

 

Regina looks skeptical as Emma opens the truck’s passenger door for her, but she climbs in anyway and awkwardly perches herself on the seat as if preparing for another drive. The blonde has to cover her laugh with a cough as she tells her to move over so she can climb in after her, moving aside the thick curtain behind the seats and turning on the light to reveal her cabin in all its tiny glory.

 

“Well. This is it,” she says, turning to Regina as the other woman takes in the small space. Between the small bench and even smaller table, the single loft bed and the minimal amenities, it isn’t much, and it certainly isn’t made for two people, but with their limited options, Emma doesn’t know what else she could do. She’s not about to sleep in one of the seats up front and then drive all day tomorrow and making Regina sleep anywhere but the bed is unacceptable.

 

Of all the questions the blonde might have expected about this situation, particularly about the bed sharing implication, Emma is surprised when Regina asks, “How does this even _work_?”

 

“Oh. I have a pretty good APU.” At Regina’s blank look, Emma elaborates. “It’s an auxiliary power unit. I could show you, but I think you’d find it pretty boring.”

 

The brunette nods, accepting the answer at face value. “So, we’re sharing the bed,” she says, and Emma chokes out an answer in the affirmative, looking anywhere but at Regina. “Okay.”

 

Where the blonde might have expected the other woman to put up a fight—their trip together so far hadn’t been exactly _pleasant_ —Regina surprises her with the casual acceptance of their sleeping situation, which of course, was something that still had Emma in a panic. She slips from the cabin to the front of the truck to give Regina some privacy, changing into whatever she’s sleeping in (Emma had been planning on donning the t-shirt and boxers look) and hoping for the best. When she hears the brunette climbing the ladder up to the bed, she moves past the curtain once again, and turns off the lights before taking off her pants and bra and following Regina up.

 

The bed isn’t very big—not even the size of a standard single mattress—but there’s still enough room for the two of them, except that the bunk doesn’t have a guardrail to stop Emma from falling off.

 

“You don’t kick in your sleep, do you?”

 

Regina snorts once. “No.”

 

“Okay, good. Because I’ll probably be only a nudge away from falling off. Have you scooted over all the way?” Emma asks as she situates herself on the open end of the tiny bed. She’s fortunate enough to have had more than a few unfortunate bed sharing experiences to know that she won’t move around too much in her sleep, but that does leave her comatose fate in the other woman’s hands.

 

“Of course I have,” Regina answers with a scowl. “My nose is nearly pressing into the wall.”

 

“Sorry,” Emma dismisses, knowing there isn’t anything she can do anyway, as she settles down for the night, back-to-back with Regina and trying to ignore the fact that their asses are touching. She’s going to need to get good sleep tomorrow to drive, so she counts her breathing—in through her nose with a count to four, hold for seven seconds, out through her mouth with a count to eight, and start again. She repeats the pattern several times before she finally drifts off for the night.


	2. Day Two

**Notes for the Chapter:**

> thank you everyone for your encouraging comments! i'm really happy you guys are liking this fic, and i hope this chapter doesn't disappoint <3
> 
> and don't forget about [this cool playlist](https://open.spotify.com/user/lamestories/playlist/0DQkCqudQYlrIJPxMw3fVG?si=ZxI7krKVQRGoHREDxk6T0Q) i made to match the fic

When Emma wakes up the next morning, she’s in the exact same position she fell asleep in, and it seems Regina is as well, at least until Emma shifts. The movement spurs Regina to roll completely over and drape an arm across the blonde’s hip, which startles Emma enough to have her going over the edge of the bed and miraculously landing on her feet.

 

However, the sound that leaves her throat is less elegant, and it has Regina bolting upright on the mattress, her head narrowly missing the ceiling. “What’s happening?” she asks, her voice alert and still a little sleepy, and the sound of it makes Emma’s heart beat faster—or maybe that’s from the residue shock of nearly falling on her ass from a loft bed.

 

Emma clears her throat. “Uh, nothing,” she says, checking her watch for the time. “We should get ready to head out soon. I have some granola bars for breakfast, but we’ll have to go inside for coffee.”

 

“Okay,” Regina mumbles, managing to find her way down the ladder. “I can get it after I freshen up.”

 

“I’ll, uh, let you get dressed,” Emma says as she ducks behind the curtain separating her sleeper from the rig. She takes a deep breath as she sits down on the passenger seat (because it’s the one she never gets to sit in) and waits for Regina to make herself presentable. It only takes a couple minutes before the brunette pokes her head in. 

 

“So, coffee?”

 

“Heck yes,” Emma says, switching places so she can get dressed while Regina heads into the truck stop. She makes quick work of changing into her clothes for the day and making sure they’ll be ready to head out in the next fifteen minutes. When Regina comes back, she’s standing outside with her toothbrush, spitting a mouthful of toothpaste onto the pavement before turning to see her favorite hitchhiker standing behind her with an amused expression.

 

“You could have just used the sink inside,” she smirks.

 

“Yeah, well. I don’t really like brushing my teeth where people can see me.” At that, Regina just snorts, looking around the relatively busy parking lot as a response. “Okay, c’mon,” Emma laughs. “You know what I mean. Bathrooms are so quiet sometimes, and I don’t need anyone judging the intensity of— No, you know what? I don’t need to get into this,” she says, putting her toothbrush back in the bag resting on the hood of the truck and tossing it back inside.

 

“Okay,” Regina laughs, “are you going to pee out here, too? Do I need to turn around?”

 

“Ha ha,” Emma replies. “No, I’m gonna hit the bathroom and then we’ll head out.” She shakes her head as she walks away, but can’t seem to be anything but transfixed on the sound of the brunette’s laugh behind her.

 

They leave just after nine in the morning, and Emma feels genuinely nervous for the first time since acquiring Regina’s company. The cabin of her truck is quiet, short of the radio playing in the background, and for a good thirty minutes, all she can think about is that they have almost twenty-five hundred miles to go and how awkward it’ll be if it stays this quiet.

 

Everything changes once they get to Cleveland and Regina releases an uncharacteristic squeal followed by an apology. Emma laughs as she glances over at her before she turns back to the road, awaiting an explanation.

 

“I’ve never been this far from home before.”

 

“Seriously?” Emma blurts. “We haven’t even gone that far.” She laughs while the brunette just rolls her eyes—she can hear it in the other woman’s small scoff.

 

“Yeah,” she shrugs. “I haven’t had many travelling opportunities.”

 

At the confession and the hint of disappointment in Regina’s voice, Emma frowns. “Didn’t you ever want to? Travel, I mean? Have adventures?”

 

“Of course, I did,” she admits, her voice growing soft, almost self conscious, but she doesn’t say anything else, and Emma can feel something stirring deep in her gut. It’s half sympathy for the woman next to her, who deserves to visit interesting places as much as anyone else, and half determination, longing to help all of her wildest dreams come through.

 

When she makes her proclamation a few minutes later and immediately changes her course through the city, she attributes it almost entirely to the latter. “You want adventure? Let’s have adventure.”

 

Regina’s face lights up immediately after her initial confusion, and that alone is enough to satisfy Emma, but it doesn’t wane her desire to really impress the brunette and fulfill as many desires of hers as possible. 

 

“What are we doing?” she asks, recognizing that Emma has gone off course. “Do you know where we’re going?”

 

Emma laughs. “If I said  _ no _ , would you be worried?”

 

Regina hesitates a moment before shaking her head and laughing lightly with Emma. “I guess not, no. But  _ do you _ ?”

 

This time the blonde’s answer is a subtle smile and silence, making Regina wait and see. She knows the city well enough from one foster home she was placed in years ago, and the plan for her and Regina’s night is solely based on those memories, as well as what the internet has to suggest once they’ve made their first stop. 

 

First and foremost is parking, which is already hard enough in the city in a  _ normal  _ car, not to mention a  _ truck _ , but she manages before walking around the side of the vehicle to help Regina out. The brunette doesn’t look impressed with their surroundings (and honestly, Emma can’t blame her because they’re in a parking lot), but her eyes are bright nonetheless as she takes in the surroundings, old to the city but new to her.

 

“Ready to go?” Emma asks, and Regina nods as she follows Emma from the parking lot.

 

“So where are we going?” she asks, and the blonde turns around enough to smirk at her. 

 

“It’s a surprise,” she says, and Regina frowns, which only makes Emma’s smile widen. She’s excited about their day to come, and she hopes Regina will be, too.

 

The walk to their first location is brief; they don’t talk much along the way, but from the way Regina fidgets her hands, Emma can tell the brunette’s anticipation for the trip is at a high, either from excitement or nerves. Honestly, she feels nervous as well. She has history in this city, and even if she isn’t planning to share it, Emma knows that it’s bound to come up sometime today.

 

“Well. Here we are,” Emma says as they finally approach their destination. She holds out a hand to display the building, even though the action is cliche, and going by the look on the brunette’s face, their visit doesn’t require such an introduction. Regina’s jaw is hanging open as they approach the entrance to the International Women's Air & Space Museum. “I used to come here a lot when I was a kid,” Emma says, kicking herself for starting to say anything too personal when she had  _ just _ been thinking about how she wasn’t sure she wanted to open up about anything. But really, it’s inevitable, and a part of her realizes that.

 

As they step into the building, Emma is overwhelmed by the sense of nostalgia she feels at seeing a place she remembers so much of but hasn’t seen in over a decade. Regina seems to be experiencing her own sense of wonder as she takes in everything from the entrance to the first exhibits, and the two remain silent as their journey through women’s aviation history begins.

 

“You said you came here when you were a kid?” Regina eventually asks, and Emma tenses at the question on instinct, not used to talking about her past so casually. It takes some self-assurance and the reminder that she’s doing this for Regina to get her to a place where she feels comfortable opening up.

 

She nods as she explains, “The first time we came here, it was on a field trip, but I liked it so much that I found ways to come back on my own.”

 

At first Regina just nods, accepting the answer at face value, but eventually she asks, “Why?” It’s a question that doesn’t necessarily need answering considering how awesome this place is, but Emma knows that Regina isn’t asking because she doesn’t know why anyone would come here—the amazement written on her face tells Emma that she already knows the general answer to such a question—she’s asking because she wants to hear Emma’s story.

 

“It’s amazing,” is the start to Emma’s answer, on the verge of generic. “I grew up thinking I wouldn’t become much of anyone, but everytime I came in here and saw these incredible women and what they accomplished, I couldn’t help but wonder if they ever thought the same thing whenever they were kids—if they ever doubted themselves. But look at what they did,” she says.

 

Regina hums as she observes the wall featuring portraits of all the women of space.

 

“I wanted to bring you here because you talked about not knowing what you want to do with your life. I don’t know if you ever worry about it as much as I do, but even if you don’t, there’s a lot of empowerment and inspiration here. I know I can’t fix anything, but it’s the least I can do.” Emma shrugs, a little embarrassed by her tangent until she feels Regina’s hand slip into hers, squeezing once just lightly before letting go.

 

“Thank you,” she says.

 

It’s more than enough for Emma.

 

For the remainder of their time in the International Women’s Air and Space Museum, the two of them remain quiet, just reading and observing all the museum has to offer until they’ve seen it all and stepped outside once more. “Now what?” Regina asks.

 

“I’m glad you asked,” Emma smiles back at her as she leads her back down the street. It’s a minute before Regina catches up to her, and the blonde imagines her frowning in confusion as she watches Emma walk in the opposite direction from where they parked. “It’s only a short walk away,” Emma grins back at her.

 

Regina catches up, and they walk side by side toward the next destination, their shoulders bumping just slightly as they go. Emma waits for more questions from the brunette, but they don’t come, and by the time they’re standing in view of the Rock and Roll Hall of Fame, Regina’s jaw is slack as she admires the building’s unique architecture. “What do you think?” Emma can’t help but ask, knowing she isn’t going to get much of a verbal response.

 

She doesn’t, but once they get inside, Regina doesn’t stop talking, pointing out a few things she recognizes and even more things she didn’t know about, clearly excited about learning more of a world she’s never been a big part of. 

 

“Did you come here a lot, too?” 

 

Emma shrugs, “Just once, but I remember really liking it. It was one of the first places I thought of when I decided we were making this city detour.” The mention of planning has Regina beaming, and Emma has to look away to hide her blush. She still doesn’t know the woman  _ that _ well, but she still manages to have this unexplainable affect over her (not that Emma is complaining). 

 

They spend more time in the Rock and Roll Hall of Fame than in the previous museum, mostly because Regina has more questions than Emma ever imagined one person could possibly have, but eventually they’ve seen everything it has to offer and head back to the truck.

 

“The next place isn’t as close,” Emma explains, as if worried that Regina’s going to grow impatient about all the little stops along the way, but all she does is smile at the blonde like she doesn’t mind in the least. 

 

The smile remains on her face long after they’ve started the next short trip, and when Emma parks again, Regina is the first out of the truck. Emma laughs at her enthusiasm, and the brunette shrugs. “You only have yourself to blame for getting me so excited about this. I don’t even know where we’re going.”

 

“You’ll see,” Emma smirks as they start out on another short walk, glowing with pride as they finally make it to their next destination, and this time, Emma thinks their location deserves the fanfare of her dramatically throwing both arms out with a full fledged  _ ta da! _

 

Despite the grand introduction, Regina just stares straight forward, her brows furrowed as she stares at the house. “What is it?” she asks.

 

Emma gapes. “ _ What is it? _ Regina, are you serious? Have you never seen  _ A Christmas Story _ ?”

 

“I’ve heard of it...” the brunette offers, and Emma just gapes more. “What? It’s not that big a deal, is it?”

 

“Not that big a deal?” Emma questions in a low voice, completely appalled. “It’s a  _ classic _ , Regina. You have to have seen it!” When the brunette shakes her head, answering the question once more, Emma throws her hands in the air before dramatically turning back around. “ _ Well _ ,” she starts, “we’ll watch it sometime then.”

 

“When?” Regina laughs. “Soon enough we’re going to be on opposite sides of the country. It’s not very conducive for movie nights.”

 

“Yeah,” she shrugs. She knows the end of their short term friendship isn’t that far down the road (figuratively, anyway), but she isn’t ready to think that far into the future when there’s still so much left for them to do over the next week. “We’ll cross that bridge when we get to it. In the meantime, get ready to see the best house ever.”

 

The tour is as great as Emma remembered it, and even though Regina doesn’t understand her jokes, her references, or anything she rattles on about, they both have a good time. “See? Now you really want to watch it, right?”

 

“Sure,” Regina says, laughing at Emma’s near horrified expression at the casual answer. She laughs, bumping into the blonde playfully. “I’m  _ kidding _ . I can’t wait to watch it with you.”

 

“Oh thank god,” Emma jokes back. “I might have had to leave you here in Cleveland.”

 

“Well, then I would have had to hunt you down in LA. Or on the road back,” she adds. She’s now turned to face Emma, a soft smile on her face that makes Emma blush. “So,” she starts again after a moment. “What’s your favorite movie? Besides  _ A Christmas Story _ , that is.”

 

“Goonies,” Emma answers easily, but falters when she sees the blank look on Regina’s face. “Oh my god, you haven’t seen that either have you?”

 

“Does our friendship depend on my answer?”

 

“Of course,” Emma answers, grinning at the words  _ our friendship _ .

 

“Then, yes.” They laugh together for a moment as they start to head back to the truck, Emma’s heart glowing at the thought of Regina considering that they have friendship enough to lie about having seen Goonies. 

 

“I’m adding it to the list, I hope you realize,” Emma tells her. “So, what about you? Here I am judging you for not having seen my favorite movies, but I might not have seen any of yours. What do you like? And if you haven’t seen  _ A Christmas Story, _ I’m dying to know which movie you never fail to watch every holiday.”

 

Regina hums as though thinking before letting out a hearty chuckle. “I should make you guess.”

 

“You wouldn’t,” Emma responds in mock horror, laughing with the brunette when they bump shoulders again. She could easily imagine them walking down the street hand in hand, but she dismisses the thought as it comes. 

 

“You’re right, I wouldn’t. My favorite Christmas movie is  _ It’s a Wonderful Life. _ I watch it every year. As for movies in general, I’m a fan of the classics.”

 

“ _ Star Wars _ ?” Emma blurts.

 

“Well, yes. I  _ do _ enjoy Star Wars, but I’m thinking older. Audrey Hepburn and Humphrey Bogart. Alfred Hitchcock. Charlie Chaplin… To name a few. My father and I used to watch movies all the time when I was younger. I suppose his taste rubbed off on me. Not that I mind, of course.”

 

The way Regina talks about her father is almost wistful, and Emma suddenly worries about how she should phrase her next question. She goes for something more open ended than what she’d been originally planning to ask. “Do you still watch movies with him?”

 

The brunette offers up a sad smile as she shakes her head. “No. He passed away a few years ago, right after I graduated from university.”

 

“You must miss him a lot, huh?” Emma asks, wishing she knew what to say to make this better.

 

“I do,” Regina confirms. “He was my favorite person. I think his passing was what really made things tough between my mom and I. She never seemed to mourn him like I did, almost like she couldn’t see where my grief was coming from. Every resentment I ever held for her just got worse after that.”

 

The two fall into silence after that, Emma not knowing quite what to say and Regina being content with them just walking together. She frowns as they pass the place where Emma had parked, but doesn’t ask when she notices the grin on Emma’s face.

 

“There’s one last place we’re going to visit before getting back on the road,” she explains, gesturing to a quaint little building amidst the rest of the chaos around them. “I used to come here after school when I lived in Cleveland. The owner was kind of like a mother to me.”

 

If Regina had any thoughts on Emma’s choice of words with  _ a mother _ as opposed to  _ another mother _ (as she was sure many people would have said), she doesn’t comment. Emma’s grateful for that since she doesn’t think she’s ready to launch into the foster home backstory with Regina yet. Instead the brunette just smiles. “Does she still work there?”

 

“Yeah, I think so.” Honestly, Emma wasn’t sure. She’d looked up the diner online and had reason to believe nothing had changed since her last visit years ago, but she couldn’t say for sure. “I hope so.”

 

They approach  _ Grumpy’s Diner _ in the next few paces, and Regina’s eyes light up as she looks at it. “It looks like one of those places you see in movies. A  _ classic diner _ ,” she calls it. 

 

“Just wait,” Emma laughs as she pushes the door open. The diner is stereotypical of a  _ classic diner _ from the outside, but the inside, even more so. It has the black and white checkered floors, the retro tables, chairs and booths, the neon signs, and even a bartop with stools to match. It’s all exactly as Emma remembers it, and as soon as the nostalgia comes back, Emma has a wide smile plastered on her face. Nothing has changed, not even—

 

“Emma!” She hears a chipper voice call out, and as the blonde rushes over to the counter, her smile grows. She pulls Regina gently behind her, only thinking in retrospect about them holding hands, but she doesn’t mind, and it doesn’t seem like the brunette does either.

 

“Mary Margaret! Hey!” Emma greets before turning to Regina. “Regina, this is Mary Margaret, the owner of Grumpy’s Diner. Mary Margaret, this is Regina.”

 

“Oooh,” the other woman says, wiggling her eyebrows. “Girlfriend? You two are so cute together!” she continues before Emma can correct her. “Well, whatever you’re getting this evening, it’s on me.” 

 

She practically skips away to get their drinks, leaving them at the bartop with a pair of menus and an awkward silence. “Sorry,” Emma says sheepishly. “She’s a little intense.”

 

“That’s one word for it,” Regina snorts. “But it’s fine. I do have one question though.” Emma nods, bracing herself for whatever is to come. This question could be anything, and if Regina’s mind is anywhere like Emma’s is, she’s thinking about how Mary Margaret thinks they’re a couple.

 

“This place is called  _ Grumpy’s Diner _ , but that woman seems anything but. You said she owns this place?”

 

The skepticism in Regina’s voice makes Emma laugh as she answers, “Yeah, and she established it. It’s a bit of a misnomer, but Mary Margaret has this whole thing about defying expectations. It’s been around for almost twenty-five years now, I think.”

 

“You’re not bragging about me, are you, Emma?” Mary Margaret asks as she reappears. Emma starts to make up an excuse, but the diner owner waves it off with a cheery grin. “You know I don’t mind.” She takes their orders, both grilled cheeses, (“Mary Margaret has the best grilled cheeses ever,” Emma assured. “Bacon, tomato, and at least four different kinds of cheese!”) and heads back to get the meals ready.

 

Emma goes on and on about the food for a while, asking Regina the most important food related questions—her favorite meals of all time, comfort foods, least favorite flavors, allergies, and by the time the renowned grilled cheeses are in front of them, Emma feels like she knows Regina even better than she had when they walked in here.

 

“So,” Mary Margaret drawls, an expression on her face letting Emma know that she’s about to get nosy, “How’d you two meet?”

 

“Uh,” Emma starts, wondering how she’s supposed to tell a story with such odd circumstances  _ and _ break the news that she and Regina are just friends (of only a couple of days at that), when the woman next to her jumps in and runs with the story on her own.

 

“I was hitchhiking, and Emma picked me up on the side of the road in her truck. We’ve been attached at the hip ever since,” she says, draping her arm around Emma for good measure. Mary Margaret seems to think the entire thing is just  _ too cute _ , and goes on about how she didn’t realize Emma had become a trucker. She has a whole list of curious questions for her about it, but Emma can’t seem to answer any of them beyond a few feeble nods and muttered responses, especially not when Regina is  _ definitely _ pretending to be her girlfriend.

 

And why? Emma doesn’t know, but it’s certainly all she can think about.

 

She’s still thinking about it when they have to leave the diner, and as she hugs Mary Margaret goodbye and hears her supportive whisper (“I like her, Emma. She’s a keeper.”), it’s like there’s no point in any other thoughts going on in her mind.

 

“Come back and visit!” Mary Margaret calls after them. the two wave back, and Emma is still so distracted that she doesn’t realize Regina’s holding her hand until she drops it when the diner is no longer in sight.

 

“That was so much fun,” Regina says, a huge smile on her face. There’s something different about the way she’s walking, lighter and more carefree, and if anything pulls Emma out of the thoughts on what it feels like to hold Regina’s hand, it’s the clear difference in Regina’s mood in only a day. “Thank you so much, Emma,” the brunette tells her. “I don’t think I’ve enjoyed myself this much in a long time.”

 

“Oh yeah? Just wait until tomorrow,” Emma finds herself saying. She doesn’t actually know  _ what _ is going to happen tomorrow, but she plans on making it just as good, if not better, than today has been.

 

She has a lot of driving to make up for, especially when she plans out their next day activities while at a stop along the way. Dinner comes shortly after, and it’s nothing very exciting (just McDonald’s) but Regina seems to think it’s the most incredible thing ever, and Emma can’t help but laugh. “You never got Happy Meals as a kid?” 

 

“No, my mother didn’t think it was good for me.”

 

“It’s not,” Emma admits with a laugh, “But it’s quick and easy when you need it.”

 

By the time they’re on the road again, it’s almost nine at night, and Emma’s starting to feel exhausted. She suddenly understands why August had told her not to drink too much caffeine after a certain time. It’s all so she can fall asleep easy at night. There’s no doubt she’ll fall asleep easily tonight.

 

It’s almost ten when Regina (who has been observing a map she picked up on a recent stop) starts fidgeting again, like she had the first night. Only this time, Emma doesn’t have to coerce information out of her. “Can we stop in Michigan?” she asks, sounding almost too excited about the idea.

 

Emma chuckles, “Yeah, sure. It won’t be a very fun trip though. Just a driving through type of deal.”

 

“That’s okay,” she says. “I just haven’t been there. I at least want to walk around on Michigan soil, or something.”

 

Up until this moment, Emma had been planning to stop just before crossing state lines, but with a beautiful woman next to her  _ this _ excited about Michigan, she can’t help but change plans on the spot. “I can do you one better,” she says. “We can stay the night there.”

 

Regina beams, and Emma has no doubt that the woman has a mental checklist going about which states she’s visited. She’s happy to help add a few to the list. 

 

They stop at a truck stop in Sturgis, and while Regina freshens up, Emma puts the finishing touches on the day she has planned for them tomorrow. Admittedly, the whole thing makes her nervous. She knows that no matter what, Regina’s going to be excited, but she can’t stop the desire to impress her companion.

 

She doesn’t really grasp  _ why _ until they’re climbing into the tiny bed of Emma’s truck cabin that night.

 

It’s colder than it was the last night, and she can both feel and hear Regina shivering behind her for a moment before the brunette takes the plunge Emma is too afraid to make herself and curls herself closer to the blonde’s body. Emma feels a strong arm pulling her closer, and she can do nothing but give in, smiling against Regina’s hair as she falls asleep.

**Notes for the Chapter:**

> let me know what you thought!


	3. Day Three

**Notes for the Chapter:**

> shout out to quan for the idea about regina stealing emma's hat, and to nicole for inspiring the reactions a certain food truck owner has to emma and regina's meet cute in this chapter.
> 
> as always, i love you guys, thank you so much for the support, and thanks for reading!

When Emma wakes up the next morning to her annoying alarm, she reaches behind to where she’s taped it to shut it off. Once that distraction is out of the way, she realizes that Regina still has an arm around her, even though it’s not nearly as cold as it was the night before, and she can’t help but want to stay right here for the rest of the morning. Unfortunately, today’s schedule is on a more strict time frame than usual if Emma wants to make today everything she plans to.

 

She’s able to coax the other woman awake today, rather than startle her by screeching her way to the floor. At first she thinks it’s going to be more successful, but really it just makes things more difficult because Regina's response is to cling tighter, still half asleep. Emma has to find a way to wiggle herself from the brunette’s grasp and out of the bed (without falling off this time). She eventually succeeds even if it means foregoing the ladder and having to hang off the bed until her feet hit something solid. Her heart is still racing after she’s safely made it down, so when Regina wakes up only moments later, Emma does her best to act normal.

 

“Hey, how’d you sleep?”

 

“Great,” Regina answers. “You?”

 

“Also great.” She stands around awkwardly, unsure what to say. They have a little more time this morning than they did yesterday before they have to leave, and it’s not like she could supply a five star breakfast, but she knows she can do one better than granola bars on the road. “Um, okay, so whenever you go inside, I’m going to get the truck refueled and get breakfast ready. We should probably head out within the hour, but we have some time.”

 

“For?” Regina asks, a little confused. 

 

“For breakfast?

 

“What, are you going to cook us something fancy?” Regina teases.

 

“Something like that.”

 

Emma rushes from the moment Regina heads inside, trying to get herself ready for the day  _ and _ refuel the truck  _ and  _ have it parked by the time the other woman has exited the truck stop. By some miracle, she manages, and as she’s headed back to set up for their “fancy breakfast,” she catches sight of Regina walking toward the truck with a cup of coffee in each hand, her toiletry bag tucked under her arm.

 

Her little microwave sounds for the second time when she hears the passenger door open, and she takes out the o _ n-the-go _ container of oatmeal to get it stirred and ready before the curtain is pulled back. When it finally is, Emma is on the side of the bench closest to the wall, an arm casually draped on the back of the bench like she’d been waiting there the entire time.

 

Regina takes one look at Emma before glancing once at the two oatmeals in front of her before laughing. “Oatmeal? Really?”

 

“What?” Emma defends. “It’s quick and easy, and it’s the  _ apple cinnamon  _ flavor. You know that’s the best one, don’t you? Besides, it’s definitely a better choice than the box of Lucky Charms I could have offered instead.”

 

“How considerate of you,” Regina deadpans, a sparkle in her eye as she holds back a smile. “Since your other seat is occupied by your stuff, I guess I’m sitting next to you, then?”

 

Emma freezes up. “Is that okay?” she asks, hoping Regina doesn’t hear her nerves as she does.

 

“Why wouldn’t it be?” she laughs, and Emma relaxes immediately. “We share a bed already,  _ and _ we pretended to be dating last night. What’s sharing a bench next to those things?”

 

“Uh,” Emma starts, her brain short circuiting as she vividly remembers the night before, from the pretending to the cuddling. “It is a pretty small bench,” she says, but Regina just giggles and tells her to scoot over.

 

“It’s your turn to be pressed against the wall,” she says. It’s an innocent enough comment, but where Emma’s mind runs with it is anything but. “So, what’s on the agenda for today?”

 

“Well,” Emma starts, eating another spoonful of oatmeal before she continues. “We have a lot of driving to do first, then after that, everything’s a surprise. You’re gonna love it though.”

 

They hit the road at the same time as yesterday, and the drive is heavy with anticipation. For Regina because every day continues to be a new mystery for her, and for Emma because…well. She’s getting very attached to the idea of putting countless smiles on Regina’s face, and not to mention, she’s getting attached to Regina herself.

 

As much as she’d tried to ward off any such feelings before they appeared, they’d come on fast and front-heavy, and they continued to burrow even deeper within her heart. There’d be no point in convincing herself she didn’t have feelings if she  _ tried _ , but she’s made attempts to reason with her feelings, rationalizing them as  _ Regina is just my best friend now and since I’ve never had a friend like this, that’s why I’m confused; I’m just lonely and am reading too much into what are obviously  _ friendship _ vibes;  _ and  _ okay,  _ so  _ maybe I do have a little crush, but it’s nothing serious. I get these all the time _ . 

 

Her explanations are rock solid—they really are—at least until Regina does something like smile at Emma, or roll down the window and let her hair blow in the wind, or laugh at Emma’s stupid jokes, or sing along with a song on the radio, or steal Emma’s trucker hat and wear it herself.

 

Even if one of those things is happening almost every second of the trip—and even when they’re not, Emma’s lost in thought about what Regina’s going to think about her plans for the day or them sharing her tiny bed—Emma manages to maintain a level of cool rivaled by the Fonz the whole drive to Chicago.

 

Two hours later, and they’re approaching the city, which has Regina staring slack jawed out the window. “Are we where I think we are?”

 

“If you’re thinking Chicago, then yes,” Emma answers with a smirk. She’s only been here once, longer ago than when she’d been in Cleveland, so she can’t deny her own feeling of excitement looking at the city as they enter.

 

“Isn’t Chicago a little out of the way? I mean, I don’t really know your route, but…” she trails off with an almost smug look that Emma can’t help but roll her eyes at. The fact of the matter is that Chicago  _ is _ way off course, but she doesn’t plan on admitting that to Regina. Besides, it isn’t so far off that it’s detrimental to her job, and she figured it would be well worth the detour. 

 

Finding parking here is even more difficult than it had been in Cleveland, and Emma apologizes in advance. “We might be walking a  _ lot _ today,” she tells her, but Regina just shrugs.

 

“Between hours sitting in the truck and walking around the city, it balances out.”

 

While Emma scrambles to pack up anything they might need for their outing, Regina waits outside the truck, a quaint smile on her face as she takes in the area around her. Emma doesn’t know this because she admired her for a moment before asking if she was ready to go or anything. “Ready?”

 

“Absolutely,” Regina responds, walking alongside Emma as she leads them toward their first stop. 12th Street Beach is only a short walk away, and with every step closer, the amount of water around them grows. By the time they’ve reached the shore, Regina’s already figured it out. “Lake Michigan, right?” 

 

In the sun, the smile on her face is brighter than ever, and Emma has to take a moment just to find her voice again to answer. “Yeah. You like it?”

 

“What do you think?” Regina asks as she raises a brow. Emma laughs and Regina soon joins her.

 

“Yeah that was a pretty dumb question, wasn’t it? Who wouldn’t like this place. It’s beautiful.” She pulls out the towel she brought as they walk into the sand, kicking her shoes off when she reaches the spot Regina had stopped at, her own toes already buried in the sand. “Here?” she confirms before spreading the towel, and offering for Regina to sit first. 

 

For a while they just sit in silence, looking at the view and relishing the atmosphere. It’s a perfect day to be here. There isn’t too big of a crowd, and the people that are around them carry an uplifting mood. Lots of smiles, kids running around laughing, couples paired off sitting on towels…(though Emma tries not to notice that last one too much). The weather is the epitome of a perfect summer day, and as a pleasant breeze rolls through, Emma glances over at Regina, still wearing Emma’s hat and donning a pair of Ray Bans.

 

“So have you ever been here before?” she suddenly asks, startling Emma slightly when she turns toward her. 

 

“Uh, yeah. Only once though, and I was really young, so I don’t remember much. Only some of the big things,” she admits.

 

“Let me guess. Those are the things we’re going to be seeing today?”

 

Regina’s still smiling, but Emma can’t help but feel nervous. “Yeah. Is that okay? I just figure since we’re only here for one day, we could limit it to…I don’t know, the  _ obvious _ things. You probably already know what they are, so it won’t be much of a surprise,” she continues to ramble until she feels Regina’s hand on hers.

 

“Emma, it’s okay,” she says. “There’s nothing we could be doing today that would disappoint me. Okay?” she asks, looking at Emma until she nods in response, at which point, Regina slowly moves her hand off of Emma’s. However, with the position they’re in, both leaning back on their hands, their fingers still brush together, close enough to be touching. “So how long do we have here? I don’t know how in depth your planning has gone, but I wouldn’t want to mess up your itinerary.”

 

“Itinerary?” Emma laughs. “Psh, I didn’t go to  _ that _ much trouble,” she says, trying and failing to play it cool. She has an entire list of what they’re doing, and how long it will take them to get to each location, provided they don’t get lost. Regina seems to know it, too, with the disbelieving look she throws Emma’s way. “Fine, fine,” she continues, defeated. “I have an itinerary. But really, it’s more of a guideline. If you wanted to stay here longer, we could. All day, even. It’s whatever you want,” she smiles, only realizing in retrospect how that offer sounded. She’s sure the guy the next towel over said the same exact thing to the girl he started kissing two minutes ago.

 

Regina doesn’t seem to mind in the least. “We’ll go with your itinerary. I can’t wait to see what today has in store for us,” she says, playfully bumping shoulders with Emma.

 

Their day is getting off to a slow start, but it’s peaceful and simple, and Emma finds herself even more excited about their plans for today than yesterday. When it’s time to leave the beach, it’s her turn to shake the sand off the towel, which leaves her relentlessly apologizing to everyone in the vicinity. She’s easily forgiven but still embarrassed. Admittedly, it makes her feel a little better with Regina laughing at her the whole time. 

 

They walk along Lakefront Trail until they reach Buckingham Fountain. Emma was planning on heading there regardless, but when Regina sees it in the distance, she grabs Emma’s hand and tugs her over. “Do you have any coins? We have to make a wish.”

 

Emma wouldn’t have thought Regina would have been much of the wishing type, but she’s helpless to anything the woman wants to do, and she’s reaching into her bag to find some spare change before they’ve even made it over there. She passes Regina a nickel, and watches as dark eyes close, thinking up the perfect wish.

 

As for Emma, she’s lost as to what she should make a wish for. Before meeting Regina, she would have easily decided on something like  _ I wish I could figure out what to do with my life _ or  _ I wish to survive this drive _ or _ I wish I had a dog _ , but now that Regina’s come into her life, everything has changed.

 

But how cliche would it be to wish for Regina to reciprocate her feelings, or even for a chance to kiss her? She wonders what Regina’s wishing for.

 

In the end, she goes with a simple  _ I wish for happiness _ , tossing her coin in at the same time as Regina. The brunette turns to face her with a smile, and Emma finds herself asking the same question so many people ask but never get an answer to. “What did you wish for?”

 

“Wouldn’t you like to know,” Regina says with a wink that makes Emma’s knees weak. “Come on, let’s go,” she says, looping her arm around Emma’s to steer her away from the fountain. She doesn’t know where their destination is, but Emma is grateful considering her legs stopped working for a moment. 

 

Of all the treks they’ll be making today, the one from 12th Beach Street to Cloud Gate is the longest, but it feels good to be out and moving around. Emma doesn’t even want to imagine the nightmare of navigating downtown Chicago in her truck, much less live it. She points out the The Art Institute of Chicago as they pass, telling Regina about how she wants to visit one day. “You would probably love it. I wanted to go today, but it seems like it would be better if we had more time.”

 

“I guess we’ll have to come back one day then,” Regina says, like they aren’t going their separate ways once this trip ends. It makes Emma wonder what she’s thinking, but she doesn’t dare ask.

 

Regina’s excitement is at an all time high once they reach Cloud Gate, and Emma’s is as well. Seeing “the Bean” is one of her more prominent memories from the Chicago visit, from being in awe at the sculpture and the sights reflected in it to goofing off for pictures. The strangers around them are unified by their experiences and laughter, letting their guard down in moments of unadulterated integration. 

 

She and Regina take turns with Emma’s phone taking pictures of each other in front of Cloud Gate and take a few silly selfies of their reflections both around and under the bean. They even have a kind woman offer to take one of the two of them together standing in front, arms around each other as they smile. “You two are a lovely couple,” the woman says as she hands back the phone and turns back to her husband. Emma blushes, but Regina looks beyond flattered.

 

She looks through the pictures they’ve taken with a wide grin. “We really do look good together don’t we?” It’s rhetorical, but regardless, it sends a shiver down Emma’s spine that she then blames on a cool breeze. “You know, windy city and all that,” she says with a nervous laugh, Regina hums like she can see right through the excuse, and for a moment, Emma hopes she does.

 

“We should be taking more pictures, you know. I can’t believe it took us three days to finally get  _ one _ . You’ll send them to me, right?” 

 

Emma nods.  _ Of course _ . They’d figure out a way. Email, probably. Regina had explained the other day that she hadn’t brought her phone with her, worried about her mother being able to track her down. It was a wild notion, especially considering she could have been picked up on the road by  _ anyone _ (“I got lucky,” Regina continues to remind her), but there was also a freedom in being unplugged, not to mention it turned all of Regina’s focus onto Emma, who didn’t mind in the least.

 

“Are you hungry?” Emma asks.

 

Regina nods. “What did you have in mind?” 

 

The plan was pizza for dinner, so lunch would be a little more low key. This was the only part that Emma hadn’t already thought up ahead of time, but when she spots a food truck not too far away that says  _ Best Tacos Ever _ , she’s completely sold. “Let’s go there,” she says, pointing it out, starting to walk over before Regina can say anything.

 

“Doesn’t that seem a little sketchy?” Regina says when she catches up. “I mean, it’s called  _ Best Tacos Ever _ . Is that even a real name? They may not even be registered to serve food.”

 

Emma laughs, “Why would they be advertising  _ Best Tacos Ever _ if they weren’t selling  really great tacos. Plus there are other people buying them,  _ and _ they even have a pride flag. See?” she says, pointing out the rainbow flag flying off to the side. “This is the perfect place. Plus we can go back and sit at those benches near Cloud Gate to eat. Everything about this is perfect. You like tacos, right?”

 

“ _ Of course _ , I like tacos,” Regina says, only half relenting to Emma’s plan. She follows the blonde all the way over to the truck, and Emma turns around just before they approach to make sure Regina’s actually good with this plan. Up close, it’s clear a lot of time and effort went into this business, even if Regina didn’t think the same could be said for the name. Emma, on the other hand, loved the name. Direct and to the point. “Okay, I guess this is good,” Regina admits. 

 

With the other woman’s approval, Emma turns and heads to the window at the exact moment the two women running the truck share a quick kiss, and Emma simultaneously feels welcome and intrusive. 

 

“Sorry,” one of them says when she notices Emma and Regina, but the other one gives her partner a look.

 

“Don’t apologize, babe. I’m sure these two understand where we’re coming from,” she says, winking at Emma, who offers a generic smile in return. “My name’s Ruby, and this is Mulan. Welcome to the place that sells the best tacos ever,  _ Best Tacos Ever _ .”

 

Her partner— _ Mulan _ —rolls her eyes before addressing Emma. “Don’t mind her. What would you two like? We have a buy two get one free special going today, and you can mix and match tacos or just get all the same kind. We also have nachos, or chips and salsa.” She passes them a paper menu from the counter. “Take your time.”

 

“Thanks,” Emma says. She already knows that she’s just going to play taco roulette and pick three tacos at random, whichever she points to first, so she reads them off so Mulan can get started before she passes Regina the menu.

 

“So, are you guys from around here? Or is this your first trip to Chicago?” Ruby asks.

 

“First trip,” Emma simply answers. “We’re actually just here for the day, passing through.”

 

“From where?”

 

“Everywhere,” Emma snorts. “I’m from Boston, but Regina’s from Buffalo. We drove here from Cleveland—or, well, Sturgis, Michigan technically.” 

 

Ruby looks confused, but she chuckles at Emma’s answer anyway. “A road trip? That’s awesome. So, you’re both from different places… How’d you meet?” 

 

Emma grins, remembering her hesitation at sharing the truth of their unique introduction to Mary Margaret and the way Regina had told the story with no reservations. This time, Emma takes a page from Regina’s book. “I’m a trucker, and Regina was hitchhiking out of Buffalo when I offered her a ride. We’ve been travelling together ever since.”

 

The expression on Ruby’s face is priceless. “That’s one of the greatest things I’ve ever heard in my entire life,” she says before turning to Mulan. “Babe, oh my god, did you hear that? These two are living right out of a fanfiction!” The woman’s girlfriend just shakes her head, laughing before she turns back to cooking. “Wow, I don’t think I’ll ever look at trucks the same after this.”

 

“Why?” Emma laughs. 

 

“Because now whenever I pass one, I’m just going to wonder if there’s a pair of adventuring lesbians in there! Even if there aren’t, it’s going to warm my heart that there  _ could _ be.”

 

Emma isn’t sure what else to say to that, so she laughs with Ruby until a moment later when Regina’s ready to order. Once she does, Ruby turns to help her girlfriend prepare the food, and Emma stands next to her non-girlfriend, wondering if the brunette heard the whole exchange. The smirk on her face tells Emma that she did. 

 

The whole time they’re waiting on their food, Emma is trying to think of  way to talk about the frequent misconception that they’re girlfriends, whether just to make sure Regina’s okay with that, or to just get an idea of how she  _ feels _ about it (and by extension, Emma), but she has no idea how to start such a dialogue. Any way this conversation could go just seems awkward. Maybe it would be better to see if Regina brings it up first, or just let it come up naturally.

 

“Here you go,” Ruby says as she passes them their tacos, served in little paper food boats with cartoon tacos on them. She points out the napkin dispenser and makes sure they don’t need any drinks. “I hope you have a great day in Chicago, and a great rest of your trip!” she says as she waves after them. 

 

Mulan waves, too. “If you ever visit again, make sure you come find us.”

 

“We will!” Emma assures, as Regina leads them back toward Cloud Gate, where they take seats side by side at the long picnic table, facing the sculpture. 

 

Emma pulls two bottles of water from her bag while Regina starts eating. “These really are the best tacos ever,” she says, only a few bites in.

 

“See? I told you they would be. We were lucky to find them.”

 

While they eat, they fall into a comfortable silence, just enjoying the city, hanging out, and having great tacos. Regina is the first to break the silence. “So you’ve been here before, right? Was it just a visit, or did you live here, too?”

 

“Yeah,” Emma nods. “I think I was about eight or so. It was just a visit. Maybe five days?” Even though she’s sure that by the end of the trip, she’ll have revealed some hard truths about her childhood, she’s being cryptic and hoping she won’t have to share too much.

 

But then:  “Do you have family here?”

 

“No.” Emma admits. “It was just a vacation I was lucky enough to go on with the home I was in at the time.” She doesn’t say anything else, letting the words sink in. But when Regina’s only response is silence, having paused from eating, Emma tries to casually shrug it off. “I don’t really have family anywhere,” she says, going back to Regina’s original question, thinking it’ll help until she hears how sad it sounds out loud. “It’s not a big deal, though. I was in foster care, but that was a long time ago.” She stops talking before she can continue rambling, but part of her wants to keep going just because she has no idea what Regina’s reaction is going to be, and if it’s bad, she’d rather fix it preemptively.

 

“I’m glad you told me,” Regina says, her hand resting lightly against Emma’s knee. “I imagine talking about this isn’t easy, so you don’t have to if you don’t want to. But I do want you to know that I’m here to listen whenever you need it.”

 

For a moment, Emma is speechless, but she finds a way to say thank you, looking into Regina’s eyes, genuine and caring as they meet Emma’s. “Thanks, Regina.”

 

“It’s the least I can do. Really. You’ve been so great with planning these special stops for me. Besides, even if you weren’t orchestrating all these detours, you’re still driving me to LA—getting me away from my mother. Honestly, I will owe you for the rest of my life.”

 

“It’s no big deal,” Emma says. “And I’m not just being modest. This is so much more fun with you around.”

 

Regina beams at Emma before they turn back to their lunch, finishing in time to head back down the streets of Chicago for their next mini adventure to Skydeck. 

 

“I hope you’re not afraid of heights,” Emma says on the way there, thinking she should have already asked the woman that, but it hadn’t occurred to her until this moment as they approach the Willis tower. “I already bought the tickets online.”

 

“I’m not afraid of anything,” Regina says as if Emma should have already figured. She laughs at the brunette, but otherwise refrains from commenting. There’s bound to be something she’s afraid of that comes up on this trip.

 

Little does she know, heights are definitely one of those things, because the minute Emma steps into the observation space, Regina makes a noise that almost sounds like a whimper. “It’s fine, Regina. Look,” Emma says, jumping on the glass for good measure. Regina makes another odd noise when she does so, and Emma feels bad for getting her so worried. “Hey, it’s okay. Perfectly steady. Ask anyone. But c’mon, you have to try coming out here at least for a minute. See the view, and we can get a picture… After that we can head right back down and find something else to do.”

 

It takes a bit of coaxing, but eventually Regina steps into the box with Emma, gripping her hand tightly the whole time. Emma tells her not to look down, and tilts her chin up so that when she finally opens her eyes, she’ll see the incredible view awaiting her. The second she does so, everything changes, and she gapes in awe at the city around her. “This is amazing,” she says, her hand still clasped around Emma’s. 

 

It’s only a matter of time before Regina starts to panic again, given where they are, but Emma does everything she can to keep the brunette from looking anywhere but down. It works well enough for them to get pictures together (because Regina isn’t leaving Emma’s side anytime soon) before heading back to ground level.

 

While they were up there, more time had passed than they realized, and now, it’s nearly dinnertime. Emma’s almost positive that Regina knows what to expect; they’re in Chicago, after all. 

 

Since they ate a late lunch, neither of them are particularly hungry yet, so they spend some time exploring downtown, heading towards the pizza place Emma has in mind for dinner. After a while, Emma’s stomach is the first to growl. Fortunately, they’ve almost reached the restaurant “It must be time then,” Regina smirks. “So. Tell me, Miss Swan. What are our dinner plans tonight?”

 

Regina calling her that sends an unexplainable heat wave through Emma’s body, and she tries to seem unphased as she laughs it off. “Wow, Miss Swan, huh?” The look in Regina’s eyes remains intense, almost sultry, and Emma reminds herself that she’s probably just reading too much into it. “We can go wherever you’d like, but I was thinking, since we’re in Chicago…”

 

“Pizza?” Regina asks, evidently excited by the prospect.

 

“Pizza,” Emma confirms. 

 

There’s an Uno’s nearby, and Emma leads the way until Regina sees the sign, which is when she takes over the remainder of the journey, her hand slipping into Emma’s so they don’t get separated. “Table for two,” she says as she approaches the host stand. The woman gives them a suggestive smile, likely noting their joined hands, as she grabs two menus and tells her coworker which table to seat them at.

 

For some reason, Emma is nervous. Thinking about their trip so far, a lot of this has seemed like a date, but most of that was in retrospect. This feels like a date  _ now. _

 

Their table is a two seater next to a window, which doesn’t help make this feel any less like a date, but she notes that she’s not sitting at this table because she and Regina were holding hands, but because there are a lot families in here that wouldn’t fit here. The hosts were just doing their job. Maybe no one even  _ noticed  _ they’d been holding hands.

 

Her thoughts are interrupted by Regina’s fingers against her wrist, alerting her to their server, whose introduction she’d completely missed. He’s looking at her expectantly, and she clears her throat before saying, “Water, please.” He nods before turning away, assuring he would be back momentarily with their drinks.

 

“Are you okay?” Regina asks, looking worried.

 

“Just distracted,” Emma answers before opening her menu and looking at the choices. “What are you thinking about getting? We could share a pizza if you’d life? I’m not very picky when it comes to pizza. Or food in general,” she admits. Regina looks thoughtfully at the menu for a moment until Emma interjects again, “Actually, you know what? You can pick out a pizza for us to share, and it’ll be a surprise. Don’t worry about it, either, because I’m not allergic to anything, and I’ve yet to find something I won’t eat.”

 

With Emma’s assurances, she decides on a pizza—the Numbero Uno deep dish pizza—suitable for their current adventure. She orders it for them after making sure all of the ingredients are okay with Emma, and once their menus are taken away, she grins across the table at Emma. “This is so great. My mother  _ never supported eating pizza _ ,” she says in a mocking voice, “but it’s always been one of my favorites. Secretly, of course.”

 

“Of course,” Emma laughs playing along.

 

Dinner is filled with easy conversation, and of course, their incredible deep dish pizza. Emma can’t get over the sheer amount of cheese in one slice, much less the whole pizza, and it’s safe to say she has a smile on her face for the rest of the night. 

 

It isn’t  _ just _ because of the pizza though, of course.

 

Too stuffed and tired to walk the two miles back to where Emma had parked, the two of them decide to navigate Chicago’s public transportation systems, figuring out how to get back to where they were by the L train. It’s a hectic process, figuring it all out, but they manage, and soon enough, they’re back to where they started and climbing into the truck, ready to start the final leg of the journey. 

 

It’s only seven in the evening, but it feels like so much later, especially once Regina falls asleep about an hour into the drive.

 

The silence is refreshing after a busy day in the city, and while Regina misses Emma’s presence, it’s nice to have some time to reflect on the day and unwind. She hasn’t had much (or any, really) time to herself since she picked Regina up. There’s nothing she would change, of course, but there is something to just existing in your own space and getting lost in your head without having to fear it. 

 

Their stop for the night is in Iowa City, and despite how sleepy Regina is, Emma can see her eyes light up at arriving in a new state, half-conscious or not. She helps the brunette up the ladder before she joins her. For the first time since picking up Regina, she has absolutely no idea what the next day’s going to bring, other than a lot of driving, but she’s excited for the time they’ll be spending together no matter what happens.

 

**Notes for the Chapter:**

> the next update will be next monday, a week from now, because i'll be posting another fic this weekend, likely on saturday.

**Author's Note:**

> tell me things that inspire me to keep writing, bc god knows i'm bad at WIPs


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